F. Lee Bailey disbarred in Florida in 2001 over his handling of shares of stock owned by a client who pleaded guilty to drug smuggling and money laundering, filed for bankruptcy in Maine. That stock also led to the dispute with the IRS, which said Bailey owed $1.9 million because of his failure to report some of the stock proceeds as income. With interest and penalties, the IRS filed liens against Bailey totaling $4.5 million, which has since grown to nearly $5.2 million.

The bankruptcy filing also lists $364,925 owed on Bailey’s Yarmouth condominium, but it also said Bailey will seek a “reaffirmation agreement,” meaning he won’t try to have that debt discharged. He also owes $40,000 on an unsecured loan from Alvin Malnik.